Methanol → HCID 67387711, compound

HRID 1467515Notes

Reaction equation

HRID 1467515 reaction equation
[CH:1](C1C=CC(CN(C)C(=O)OCC2C=CC=CC=2)=CC=1)=O.C(=NC1C=CC=C2C=1COC2=O)C1C=CC=CC=1.C[O-].[Na+].CO.[CH2:45]([O:52][C:53]([N:55]([CH2:57][C:58]1[CH:63]=[CH:62][C:61]([CH:64]2[C:73](=[O:74])[C:72]3[C:71]([C:75]([O:77][CH3:78])=[O:76])=[CH:70][CH:69]=[CH:68][C:67]=3[NH:66][CH:65]2[C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)=[CH:60][CH:59]=1)[CH3:56])=[O:54])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(OCC)(=O)CC>[CH2:45]([O:52][C:53]([N:55]([CH2:57][C:58]1[CH:63]=[CH:62][C:61]([CH:64]2[C:73](=[O:74])[C:72]3[C:71]([C:75]([O:77][CH2:78][CH3:1])=[O:76])=[CH:70][CH:69]=[CH:68][C:67]=3[NH:66][CH:65]2[C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)=[CH:60][CH:59]=1)[CH3:56])=[O:54])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 67258899HCID 67258899, compoundHCID 67261813HCID 67261813, compoundHCID 86639022HCID 86639022, compound

Product 1

HCID 67387711HCID 67387711, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of benzyl 4-formylbenzyl(methyl)carbamate (566 mg, 2 mmol) and 4-(benzylideneamino) isobenzofuran-1-one (474 mg, 2 mmol) in ethyl propionate (15 mL) was cooled to 0° C. A solution of sodium methoxide in methanol [sodium (184 mg, 8 mmol) in methanol (15 mL)] was then added dropwise. After the addition, the mixture was stirred at 25° C. for 18 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=100:1 to 10:1) to give a mixture of methyl 3-(4-(((benzyloxycarbonyl)(methyl)amino)methyl)-phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 3-(4-(((benzyloxycarbonyl)(methyl)amino)methyl)-phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (220 mg, yield 20%) as a light yellow solid. LC-MS (ESI) m/z: 535 (M+1)+ and 549 (M+1)+.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with water (10 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate (50 mL×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give crude product
  10. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=100:1 to 10:1)
  11. customto give

Sources & evidence

ORD record
ord-f5e379a76bf745d9890cc72780e88249
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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